SML0582
Hispidulin
≥98% (HPLC), α-glucosidase inhibitor, powder
Synonym(s):
4′,5,7-Trihydroxy-6-methoxyflavone, 5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one, 6-Methoxyapigenin, 6-Methylscutellarein, Dinatin, Salvitin, Scutellarein 6-methyl ether
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About This Item
Empirical Formula (Hill Notation):
C16H12 O6
CAS Number:
Molecular Weight:
300.26
NACRES:
NA.77
UNSPSC Code:
12352200
MDL number:
Product Name
Hispidulin, ≥98% (HPLC)
Quality Level
assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
white to beige
solubility
DMSO: 20 mg/mL, clear
storage temp.
−20°C
SMILES string
OC1=C(OC)C(O)=C(C(C=C(C2=CC=C(O)C=C2)O3)=O)C3=C1
InChI
1S/C16H12O6/c1-21-16-11(19)7-13-14(15(16)20)10(18)6-12(22-13)8-2-4-9(17)5-3-8/h2-7,17,19-20H,1H3
InChI key
IHFBPDAQLQOCBX-UHFFFAOYSA-N
Application
Hispidulin has been used as a calibration standard:
- in high-performance liquid chromatography (HPLC) for quantification of Clerodendrum petasites flavonoids
- in liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS) analysis
- in reverse-phase high-performance liquid chromatography with a diode-array detector (HPLC-DAD) and high-performance thin-layer chromatography (HPTLC)
Biochem/physiol Actions
Hispidulin also exhibits antiosteoporotic anti-atheromatous, antispasmodic and anticancer functionality. It exhibits inhibition on α-glucosidase enzymatic activity. Hispidulin inhibits platelet aggregation and is more effective than theophylline. It also acts as a modulator of the γ-aminobutyric acid receptor (GABA) and blocks the release of glutamate synaptosomes associated with cortical neurons.
Hispidulin is a bioactive flavonoid with a variety of effects including antiproliferative, antifungal, anti-inflammatory, antioxidative and antiepileptic activity.
Hispidulin is a bioactive flavonoid with a variety of effects including antiproliferative, antifungal, anti-inflammatory, antioxidative and antiepileptic activity. Like EGCG, hispidulin appears to activate AMPK and inhibit the PI3K/Akt/mTOR pathway. The antiepileptic activity may be due to additional activity as a benzodiazepine (BZD) receptor ligand.
Features and Benefits
This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Priscila Dabaghi-Barbosa et al.
Free radical research, 39(12), 1305-1315 (2005-11-22)
Hispidulin (6-methoxy-5,7,4'-trihydroxyflavone) and eupafolin (6-methoxy-5,7,3',4'-tetrahydroxyflavone), are flavonoids found in the leaves of Eupatorium litoralle. They have recognized antioxidant and antineoplastic properties, although their action mechanisms have not been previously described. We now report the effects of hispidulin on the oxidative
L D Zhou et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 26(2), 114-117 (2003-01-15)
To study the chemical constituents the roots of Chirita fimbrisepala. The constituents were extracted with solvent, separated and purified with chromatographic methods, identified by NMR, MS, UV, IR and physical-chemical constants. Three flavonoids mahuangchiside(I), hispidulin (II) and kaempferol(III) were isolated
A Hazekamp et al.
Journal of ethnopharmacology, 78(1), 45-49 (2001-10-05)
The ethanolic extract of Clerodendrum petasites was tested to evaluate the spasmolytic activity on isolated guinea-pig tracheal smooth muscle. The crude extract (2.25-9.0 mg/ml) dose-dependently caused relaxation of tracheal smooth muscle which was contracted by exposure to histamine. A bioassay-guided